GB1029445A - Preparation of conjugated diene polymers - Google Patents
Preparation of conjugated diene polymersInfo
- Publication number
- GB1029445A GB1029445A GB45416/64A GB4541664A GB1029445A GB 1029445 A GB1029445 A GB 1029445A GB 45416/64 A GB45416/64 A GB 45416/64A GB 4541664 A GB4541664 A GB 4541664A GB 1029445 A GB1029445 A GB 1029445A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tert
- salt
- lithium
- hydrocarbon radical
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001993 dienes Chemical class 0.000 title abstract 2
- 229920000642 polymer Polymers 0.000 title abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 6
- 239000004215 Carbon black (E152) Substances 0.000 abstract 5
- 229930195733 hydrocarbon Natural products 0.000 abstract 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- 239000011734 sodium Substances 0.000 abstract 3
- 159000000000 sodium salts Chemical class 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 abstract 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- 150000002900 organolithium compounds Chemical class 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 2
- 229910052701 rubidium Inorganic materials 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 abstract 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 abstract 1
- -1 2,21 - methylene Chemical class 0.000 abstract 1
- QUSTYFNPKBDELJ-UHFFFAOYSA-N 2-Pentanethiol Chemical compound CCCC(C)S QUSTYFNPKBDELJ-UHFFFAOYSA-N 0.000 abstract 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical class CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 abstract 1
- YEXHTFUPFXTNNP-UHFFFAOYSA-N CCC[Rb] Chemical compound CCC[Rb] YEXHTFUPFXTNNP-UHFFFAOYSA-N 0.000 abstract 1
- ZCUFTCUMEDALHC-UHFFFAOYSA-N CC[K] Chemical compound CC[K] ZCUFTCUMEDALHC-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- XNCJCXAKGWLQHY-UHFFFAOYSA-N [Li]C=CC=C[Li] Chemical compound [Li]C=CC=C[Li] XNCJCXAKGWLQHY-UHFFFAOYSA-N 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- LEKSIJZGSFETSJ-UHFFFAOYSA-N cyclohexane;lithium Chemical compound [Li]C1CCCCC1 LEKSIJZGSFETSJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- GECNIOWBEXHZNM-UHFFFAOYSA-N hexyl hydrogen carbonate Chemical compound CCCCCCOC(O)=O GECNIOWBEXHZNM-UHFFFAOYSA-N 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002685 polymerization catalyst Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 159000000001 potassium salts Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US323573A US3331821A (en) | 1963-11-14 | 1963-11-14 | Catalyst composition and process of preparing conjugated diene polymers utilizing same |
| US323567A US3294768A (en) | 1963-11-14 | 1963-11-14 | Preparation of conjugated diene polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1029445A true GB1029445A (en) | 1966-05-11 |
Family
ID=26984026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB45416/64A Expired GB1029445A (en) | 1963-11-14 | 1964-11-06 | Preparation of conjugated diene polymers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3331821A (fr) |
| BE (1) | BE655705A (fr) |
| DE (1) | DE1595087B2 (fr) |
| ES (1) | ES305897A1 (fr) |
| FR (1) | FR1426998A (fr) |
| GB (1) | GB1029445A (fr) |
| NL (1) | NL139982B (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0058217A1 (fr) * | 1979-11-20 | 1982-08-25 | Phillips Petroleum Company | Copolymère statistique et procédé pour sa préparation |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3692883A (en) * | 1969-08-29 | 1972-09-19 | Gary L Sommars | Process |
| US3954700A (en) * | 1975-07-11 | 1976-05-04 | The Firestone Tire & Rubber Company | Polymerization with organo sodium catalyst dissolved in hexamethylphosphorotriamide |
| GB1604395A (en) * | 1977-10-08 | 1981-12-09 | Dunlop Ltd | Elastomer compositions and tyre treads comprising them |
| JPS5575441A (en) * | 1978-12-04 | 1980-06-06 | Asahi Chem Ind Co Ltd | Styrene resin composition having excellent impact resistance |
| FR2498193B1 (fr) * | 1981-01-19 | 1986-03-21 | Poudres & Explosifs Ste Nale | Nouvelles associations de bases resultant de la combinaison d'un alkyl ou aryl lithien avec un amidure ou un hydrure alcalin, procede de polymerisation les utilisant et produit obtenu |
| US5292790A (en) * | 1991-07-31 | 1994-03-08 | Bridgestone Corporation | Conjugated diene series rubber compositions |
| US5523371A (en) * | 1991-12-30 | 1996-06-04 | Bridgestone Corporation | Functionalized polymer of improved hysteresis properties prepared using amino-substituted aryllithium polymerization initiators |
| US5519086A (en) * | 1991-12-30 | 1996-05-21 | Bridgestone Corporation | Low-hysteresis elastomer compositions using amino-substituted aryllithium polymerization initiators |
| US6025450A (en) * | 1992-10-02 | 2000-02-15 | Bridgestone Corporation | Amine containing polymers and products therefrom |
| US5552473A (en) * | 1992-10-02 | 1996-09-03 | Bridgestone Corporation | Functionalized polymer and rubber compositions produced from solubilized anionic polymerization initiators |
| US5674798A (en) * | 1992-10-16 | 1997-10-07 | Bridgestone Corporation | Hydrocarbon soluble anionic polymerization initiators |
| US5393721A (en) * | 1992-10-16 | 1995-02-28 | Bridgestone Corporation | Anionic polymerization initiators and reduced hysteresis products therefom |
| ES2110557T3 (es) * | 1992-10-30 | 1998-02-16 | Bridgestone Corp | Iniciadores de polimerizacion anionica solubles y productos de aquellos. |
| US5643848A (en) * | 1992-10-30 | 1997-07-01 | Bridgestone Corporation | Soluble anionic polymerization initiators and products therefrom |
| US5491230A (en) * | 1993-12-29 | 1996-02-13 | Bridgestone Corporation | Anionic polymerization initiators containing adducts of cyclic secondary amines and conjugated dienes, and products therefrom |
| US5521309A (en) * | 1994-12-23 | 1996-05-28 | Bridgestone Corporation | Tertiary-amino allyl-or xylyl-lithium initiators and method of preparing same |
| US5574109A (en) * | 1995-02-01 | 1996-11-12 | Bridgestone Corporation | Aminoalkyllithium compounds containing cyclic amines and polymers therefrom |
| US6080835A (en) * | 1995-02-01 | 2000-06-27 | Bridgestone Corporation | Aminoalkyllithium compounds containing cyclic amines and polymers therefrom |
| US5785778A (en) * | 1995-02-01 | 1998-07-28 | Bridgestone Corporation | Aminoalkyllithium compounds containing cyclic amines and polymers therefrom |
| US5496940A (en) * | 1995-02-01 | 1996-03-05 | Bridgestone Corporation | Alkyllithium compounds containing cyclic amines and their use in polymerization |
| US5623035A (en) * | 1995-07-21 | 1997-04-22 | The Goodyear Tire & Rubber Company | Process for the synthesis of rubbery polymers |
| US5677402A (en) * | 1995-09-22 | 1997-10-14 | The Goodyear Tire & Rubber Company | Process for preparing 3,4-polyisoprene rubber |
| US5534592A (en) * | 1995-09-22 | 1996-07-09 | The Goodyear Tire & Rubber Company | High performance blend for tire treads |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2856391A (en) * | 1956-01-09 | 1958-10-14 | Goodrich Co B F | Polymerization of 2-substituted butadiene-1,3 hydrocarbons with a catalyst comprising a lithium alkoxide and an alkenyl lithium compound |
| US2849432A (en) * | 1956-02-06 | 1958-08-26 | Firestone Tire & Rubber Co | Polymerization of diolefines |
| US3177190A (en) * | 1961-06-14 | 1965-04-06 | Phillips Petroleum Co | Preparing and curing compositions of terminally reactive polymers |
| US3208988A (en) * | 1961-10-24 | 1965-09-28 | Firestone Tire & Rubber Co | Polymerization of isoprene using a hydrocarbon polylithium catalyst |
-
1963
- 1963-11-14 US US323573A patent/US3331821A/en not_active Expired - Lifetime
-
1964
- 1964-11-06 GB GB45416/64A patent/GB1029445A/en not_active Expired
- 1964-11-11 ES ES0305897A patent/ES305897A1/es not_active Expired
- 1964-11-12 FR FR994686A patent/FR1426998A/fr not_active Expired
- 1964-11-13 BE BE655705A patent/BE655705A/xx unknown
- 1964-11-13 NL NL646413255A patent/NL139982B/xx not_active IP Right Cessation
- 1964-11-13 DE DE1595087A patent/DE1595087B2/de active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0058217A1 (fr) * | 1979-11-20 | 1982-08-25 | Phillips Petroleum Company | Copolymère statistique et procédé pour sa préparation |
Also Published As
| Publication number | Publication date |
|---|---|
| ES305897A1 (es) | 1965-05-01 |
| FR1426998A (fr) | 1966-02-04 |
| DE1595087C3 (fr) | 1980-07-31 |
| NL6413255A (fr) | 1965-05-17 |
| NL139982B (nl) | 1973-10-15 |
| DE1595087B2 (de) | 1979-11-22 |
| BE655705A (fr) | 1965-05-13 |
| DE1595087A1 (de) | 1972-04-20 |
| US3331821A (en) | 1967-07-18 |
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